


My Friends Will Never Love Me Like You

by starrynightdeancas



Series: Dean and Cas Bingo [2]
Category: Supernatural
Genre: Bottom Dean Winchester, Boys Kissing, Castiel Has a Crush on Dean Winchester, Castiel and Dean Winchester Being Idiots, Castiel and Dean Winchester Need to Use Their Words, Castiel/Dean Winchester Mutual Pining, Dean Winchester Has a Crush on Castiel, Developing Castiel/Dean Winchester, Developing Relationship, Domestic Castiel/Dean Winchester, Domestic Fluff, Feels, Fluff, Friends With Benefits, Friends With Benefits To Lovers, Friends to Lovers, Friends with Benefits Castiel/Dean Winchester, Idiots in Love, Implied Sexual Content, Kissing, M/M, Meddling Sam Winchester, Men of Letters Bunker (Supernatural), Mutual Pining, POV Sam Winchester, Pining Castiel (Supernatural), Pining Dean Winchester, Sam Winchester Ships Castiel/Dean Winchester, Sam Winchester is So Done, Wingman Sam Winchester, deanandcasbingo
Language: English
Status: Completed
Published: 2020-08-27
Updated: 2020-08-27
Packaged: 2021-03-06 15:33:54
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26131201
Author URL: https://archiveofourown.org/users/starrynightdeancas/pseuds/starrynightdeancas
Summary: Sam is tired of seeing Dean and Cas do this dance where they pretend they're happy being friends with benefits when they both clearly want more. And what kind of little brother would Sam be if he didn't meddle a little and help nudge their relationship in the right direction? Sam comes up with a plan, and throws a hypothetical scenario at Cas during a conversation, hoping the angel will take the bait and realize that Dean wants him just as much as Cas wants Dean.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Series: Dean and Cas Bingo [2]
Series URL: https://archiveofourown.org/series/1832392
Comments: 15
Kudos: 203
Collections: Dean and Cas Bingo





	My Friends Will Never Love Me Like You

**Author's Note:**

> Written for the DeanandCas Bingo
> 
> Square filled: Friends with Benefits

“Please tell me you’ve finally grown a pair and asked him already,” Sam said from the kitchen counter, flickering his gaze from the smoothie machine in front of him to look at Dean, who was slumped against the kitchen table.

“Asked him what, Sammy? Sure, you know what, last night when he was pounding me into the bed, I stopped him and asked if he wanted to be more than just friends with benefits. You got me there,” Dean said, dragging his cup of coffee up to his lips and taking a long sip.

“First of all, way too much information. Thanks for mentally scarring me for the rest of my life. Secondly, would the two of you just get your heads out of your asses? He wants you. You want him. Cut this ‘friends with benefits’ crap,” Sam said, dropping a handful of strawberries into the mixer before leaning against the counter to look at Dean.

“Trust me, I wish I could. Every single time I’ve broached the idea of something more, he shuts down. The last time I tried, he left me mid-fuck and never came back,” Dean grumbled.

“Once again, too much detail. I really don’t want to know about what you do in bed with Cas.”

“Then why do you keep hedging with this conversation?” Dean snapped, looking over at Sam with a steely expression.

“Because, Dean. You’re miserable,” Sam sighed.

“I’m not miserable. I get laid almost every night,” Dean huffed, staring down into his coffee to avoid looking up at Sam.

“And you clearly want more. What is it with you two never being able to use your words?” Sam huffed as he pressed the blend button and watched the fruits whirl down and mix with the yogurt.

Dean shrugged, taking a single bite of bacon before standing up and dumping the rest into the trash. “He doesn’t want it, Sam. If a casual fuck is all he wants, then that’s better than the alternative of not having him at all.”

With that, Sam watched Dean as he left the kitchen, shoulder slumped in defeat. As he poured his smoothie into a glass, Sam decided it was time to intervene. Dean would thank him for it later. Usually he saved his meddling younger brother antics for prank wars, but this time Sam knew Dean and Cas just needed a little push. And if he could do it in a teasing little brother way, well then Dean would be none the wiser over his little plot.

~

“Heya, Cas,” Sam said, dropping down in the seat across from him in the library two days later.

“Hello, Sam,” Cas said, looking up and flashing him a smile before glancing back down at his book. “Can I help you with something?”

“I was just wondering. You’ve been living on Earth for close to ten years now. You’re pretty familiar with the way humans interact and do things now, right?” Sam asked carefully.

Cas cocked his head, closing his book with a  _ thud _ so he could give his undivided attention to Sam. “Yes, I’d like to think I’ve learned how to integrate and understand how humans function. What are you getting at?”

“Well, you see, hypothetically speaking, I’ve been seeing someone-” Sam started to say.

“When did this happen? Does Dean know?” Cas immediately interrupted.

Sam shot Cas a look, but he threw in a grin just to sell his story. “No, Dean doesn’t know. Not yet. It’s kinda… complicated.”

Cas frowned. “How so?” he asked, leaning forwards on the table.

Sam had to bite the inside of his cheek to stop himself from smirking. ‘Gotcha,’ he thought to himself.

“Well, we’ve been hooking up for a while now, me and this person. And I really like them. But when I started seeing them, it was just casual, you know? I just went along with the casual thing because I thought it was what they wanted,” Sam explained.

“Are you talking about Eileen?” Cas asked, raising an eyebrow suggestively. God, he really had been spending too much time with Dean to have perfected that cocky look.

“It’s hypothetical,” Sam said, then deliberately ducked his head down for a moment so his hair dropped into his face.

“It is Eileen! I knew it,” Cas cheered.

‘Oh you are too easy, Castiel,’ Sam thought to himself. “Shh! Don’t say anything,” Sam said, dropping his voice into a hushed tone, as if he were telling Cas a secret.

Cas mimed zipping his lips, which was just so human in nature it made Sam smile a real smile, laughing at Cas’ antics. It was almost impossible to imagine Cas as the stoic angel they’d met a lifetime ago. With actions like that, Sam honestly wasn’t surprised his brother had fallen so hard for the angel. Talking of… back to the plan.

“So this thing between this person and I,” Sam said, raising an eyebrow as if he were letting Cas in on the secret to his lovelife- which was honestly something he’d have to deal with after he’d got Dean and Cas past this friends with benefits ordeal, because Eileen really was someone he saw a future with- “I like them. I mean we’ve been hooking up for so long now, and when we’re together it feels like there’s always something more bubbling underneath the surface, you know? But every time I broach the subject of us being more, they get spooked and close off,” Sam said, dropping his head again as if he were pained by the thought.

Cas’ hand instantly reached out to rest against his own in a comforting touch. “Have you tried sitting down and talking with her?” Cas asked.

Sam shook his head, adding on a sigh at the end for dramatic effect. “Talking hasn’t really been a speciality of ours. Not because she’s Deaf. It’s just… that we’ve spent so long dancing around each other, that I’m not sure how to talk about wanting to make things official between us without making it weird. She’s my best friend, you know?”

Cas hummed quietly for a minute, as if he were pondering what to say. “You like her?”

“Yeah, Cas, I really do,” Sam said.

“And you think the feelings are mutual?” Cas asked carefully, choosing his words.

‘Ding, ding, ding, ding, ding. There you go, Cas. Catch my drift, c’mon man,’ Sam internally begged. Sam looked up, dipping his head until he could catch Cas’ gaze. Once their eyes were locked, Sam nodded. “I’m 110% sure the feelings are mutual. Without a shadow of a doubt; no questions or hesitations.”

Sam waited with bated breath, biting at the inside of his cheek as Cas’ eyebrows scrunched; his deep-in-thought face that Sam had heard Dean call cute on more than one occasion. After a solid 60-seconds of not saying anything, Cas finally spoke. “If you sat down with Eileen, and told her how you feel, do you think she would be receptive? If you showed her how you really felt and told her that you wanted more than just a casual hook up after a hunt?”

Sam instantly nodded. “Yeah, I honestly do. It’s just working up the courage to have that conversation and laying all my cards on the table, if you catch my drift?”

Cas nodded slowly, his eyes getting a glazed far-away look to them. Sam knew his work here was done. He’d sown the seeds into Cas’ head; given him the little push he needed to finally cross that line with Dean.

Standing slowly, Sam reached out and patted Cas on the forearm. “Thanks for the advice, Cas. I think I’m going to go and call Eileen and see where things go,” Sam said carefully, waiting for Cas’ reaction.

Cas nodded, mumbling something along the lines of, “That’s a good idea.”

Patting Cas’ arm one more time, Sam slipped out of the library, smirking in victory. Now just to wait and see if Cas took the bait and followed his own advice he’d given Sam. In the meantime, calling Eileen did actually sound like a good idea. Now he’d gotten the ball rolling for Dean and Cas to finally stop playing this game of sleeping together under the connotation it meant nothing, he could finally ask Eileen out on that date he’d been promising her for weeks.

~

A week later, Sam was convinced his ears might be getting an infection from how long he’d been wearing headphones around the Bunker. In the days following his conversation with Cas, somehow the noises coming from Dean’s room had only gotten louder. There were only so many times Sam could hear Dean shouting out Cas’ name in ecstasy before he just couldn’t take it anymore and had to muffle as much sound as possible. The two of them seemed to walk around the Bunker, pleased little looks on their faces, and Sam wasn’t sure if that just meant they’d had a damn good round in the sack, or if they’d finally had that conversation.

He got his answer a few mornings later. Cas was in the kitchen early, coffee maker on and two cups waiting by the machine; Dean’s shirt from yesterday hanging open across his shoulders.

“Heya, Cas,” Sam said casually, finally glad to have caught the angel alone. He was just curious if his meddling had worked, that was all. Any details beyond that were not something Sam wanted to know, thank you very much.

“Hello, Sam,” Cas said, tone soft and warm despite his messily tired appearance.

“I was just going to ask you-” Sam started to say, but he broke off as Dean shuffled into the room.

Sam watched as his brother zeroed in on Cas, immediately walking up to him and leaning his weight onto Cas’ back, nuzzling his nose into Cas’ hairline on his neck. “I woke up and you weren’t there,” Dean mumbled tiredly, nosing down to the juncture of Cas’ jaw.

“I was making you coffee. Thought you’d be thirsty and I know how much you hate mornings unless you’ve had a cup of coffee in bed,” Cas replied, his hand coming to settle on Dean’s arm, which had slipped around Cas’ waist and rested across the angel’s stomach.

“God, I love you,” Dean murmured, kissing behind Cas’ ear, causing the angel to shudder.

Cas seemed to suck in a breath at the words, and Dean kissed him again, this time on Cas’ jawline. “Never gonna tire of telling you,” Dean said, his voice so soft that Sam almost missed it.

He didn’t miss the way Cas turned around in Dean’s embrace, leaning forward to kiss Dean long and slow until the coffee maker dinged. “Love you, too,” Cas said, and even from the other side of the kitchen, Sam could see how happy they both looked; Cas beaming at Dean and Dean tucking his head against Cas’ shoulder.

It was domestic and sweet, and everything Sam knew the two of them could be once they’d let go of the ‘friends with benefits’ game.

“Well, it’s about damn time. I was getting old waiting for you two to finally get your heads out of your asses,” Sam finally piped up.

He smirked victoriously when Dean whipped around, a look of surprise and horror on his face. “How long have you been there?”

“Long enough to see you two finally acting like a couple. Not that I’m surprised, judging by the amount of noise I hear coming from your room, I expect medical coverage for the amount of time I have to spend walking around my own home in headphones.”

Dean scowled, but the look instantly melted off his face when Cas slipped a warm cup of coffee into his hands and pressed a lingering kiss to the edge of his mouth. 

Dean tilted his head, catching Cas’ neck with his free hand and dragging the angel into a proper kiss. “Much better,” Dean hummed against Cas’ lips before pulling away.

“And you,” Dean said, pulling away from Cas to point at Sam. “I know what you did. Meddling ass of a brother. You deserve to hear us being as loud as we please when Cas fucks me into the mattress.”

“You can prove nothing. Also, fuck off, I don’t wanna hear any of the details,” Sam said smugly, sticking his middle finger up at Dean playfully.

“Watch your back, Sammy. Or maybe watch your toothbrush,” Dean said, a wicked smile crossing his lips and he grabbed Cas’ hand and started to tug the angel back towards his room.

Sam caught Cas’ eye at the last second, throwing the angel a wink and earning a full blown smile from Cas before he was gone.

Job successfully completed, Sam grabbed one of his smoothies from the fridge, pulling his phone out as he sat down at the table. He couldn’t wait to tell Eileen that his plan had worked and Dean and Cas were finally more than just casually hooking up.


End file.
